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Synthesis and Functionalization of N-Heterocycles Using Transition Metal-Free Cross-Dehydrogenative Coupling (CDC) Approaches

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Heterocycles via Cross Dehydrogenative Coupling

Abstract

The creation of carbon–carbon bonds for the construction or the post-functionalization of various N-heterocycles is one of the most active research areas in organic chemistry. Among those approaches, cross-dehydrogenative coupling (CDC) processes in the front line because of its simple, practical applicability in organic synthesis. Historically discovered in the presence of transition metal catalysts, this decade witnessed great progress in the metal-free CDC approaches, thus improving the sustainability of this transformation. This chapter aims at providing an update on selected examples of the metal-free approaches toward the access to various N-heterocycles. The first part deals with the synthesis of N-heterocycles by metal-free CDC approaches in the presence of stoichiometric or catalytic amount of oxidants, whereas the second part is focused on the last stage C–H bond functionalization of N-heterocycles via CDC process.

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Abbreviations

[bpy]I:

1-Butylpyridinium iodide

2-tert-Bu-AQN:

2-tert-Butylanthraquinone

BPO:

Benzoyl peroxide

DCP:

Dicumyl peroxide

DDQ:

2,3-Dichloro-5,6-dicyano-1,4-benzoquinone

DTBP:

Di-tert-butyl peroxide

IL:

Ionic liquids

KHMDS:

Potassium hexamethyldisilazide

mCPBA:

meta-Chloroperoxybenzoic acid

NBS:

N-Bromosuccinimide

NHS:

N-Hydroxysuccinimide

NIS:

N-Iodosuccinimide

PIDA:

(Diacetoxyiodo)benzene

PIFA:

[Bis(trifluoroacetoxy)iodo]benzene

TBAB:

Tetrabutylammonium bromide

TBAI:

Tetrabutylammonium iodide

TBHP:

tert-Butyl hydroperoxide

TEMPO:

(2,2,6,6-Tetramethylpiperidin-1-yl)oxidanyl

TFA:

Trifluoroacetic acid

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Authors and Affiliations

  1. Department of Organic Synthesis and Process Chemistry, CSIR—Indian Institute of Chemical Technology (CSIR-IICT), Hyderabad, 500007, India

    V. Murugesh & Surisetti Suresh

  2. Academy of Scientific and Innovative Research (AcSIR), Ghaziabad, 201002, India

    V. Murugesh & Surisetti Suresh

  3. Univ Rennes, UMR 6226 (Institut Des Sciences Chimiques de Rennes), 35000, Rennes, France

    Apurba Ranjan Sahoo & Mathieu Achard

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  1. National Institute of Pharmaceutical Education and Research, Guwahati, Assam, India

    Ananya Srivastava

  2. Indian Institute of Technology Guwahati, Guwahati, Assam, India

    Chandan K. Jana

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Murugesh, V., Sahoo, A.R., Achard, M., Suresh, S. (2019). Synthesis and Functionalization of N-Heterocycles Using Transition Metal-Free Cross-Dehydrogenative Coupling (CDC) Approaches. In: Srivastava, A., Jana, C. (eds) Heterocycles via Cross Dehydrogenative Coupling. Springer, Singapore. https://doi.org/10.1007/978-981-13-9144-6_5

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